Different genre, but for me these two have some similarities when it comes to the vibe they give.
As I wrote in my review for My Sweet Mobster, it is kind of like the scriptwriters didn't take themselves too seriously, which resulted in some lighthearted humor.
Both of these shows also showcases underlying issues; for MSM it is ex-convicts' struggles to get back into society, and for KF it is widows' status during Joseon times.

If you are a foodie, both of these series have a lot of food related scenes.
Other than that, Chocolate is likely to make you emotional and maybe cry, whereas Dating in the Kitchen has more "run of the mill" plots in the script, and will likely leave you with a more "warm, fuzzy feeling".

Both are coming of age-dramas, quite easy on the mind (comfort-dramas), following a group of friends, and with a somewhat awkward female protagonist.

Coming of age, school-drama, finding love, transitioning into adulthood and friendship.
Slow-paced, no extremely vicious people, although there are elements bringing dynamics to the story.

Mature career women in a workplace setting, tackling obstacles both at work and in life, and finding love without looking for it.

Stand or Fall follows the female protagonist and her two friends, whereas The Rational Life centers more around only the female protagonist.
In SoF it is "enemies to lovers", in TRL it is opposite age-gap.

Both are "historical romcoms" – funny and charming.
Both have strong female characters, although they are in very different roles.

These two dramas might not appear very similar from the synposises, but they are both a mix of workplace/mature relationship dramas with strong female characters.

Where "Sunshine of my life" revolves mostly around the main protagonist, "Stand or Fall" also follows the storylines of her two friends.

Both are what I like to call "healing dramas"; overcoming something, or finding a new path in life.
You connect with the characters, and avoid the extremes from plotting and scheming.

Some of the similarities are independent, confident career women, not plot-heavy or too extreme scheming characters, but rather depicting a more recognisable character gallery and situations that seem more plausible.
Both stories also contains something around how events during childhood can effect a person.

Both of these dramas fall into the group of "growing up, slice-of-life, love and friendship".
It's a while since I watched When I fly ..., but I remember it left me with a strong impression, as did You are Desire.

The main similarities between these two are career women meeting younger men, and the challenges the "opposite age gap" leads to.
Where "Encounter" has a bit more plots to it, Sunshine by my side is more "slice of life", I would say.

Booth series contains action and fight scenes, friendship and struggles, but the main reason I believe you might enjoy Bloodhounds if you liked D.P., is because they both contains some underlying more serious topics as well.